Zakynthos, Greece

With a population of just 41,180, Zakynthos is a Greek island that attracts hordes of British tourists each summer. However, the mild Mediterranean climate and plentiful winter rainfall come with a price - the island is prone to destructive earthquakes, including a 7.3-magnitude tremor in 1953 that devastated much of the infrastructure. Bureaucracy can also be a persistent headache, as evidenced by the island's complex administrative history, changing hands between the Venetians, French, British, and finally Greece over centuries. While Zakynthos offers a scenic seaside getaway, its natural disasters and red tape make it best suited for the adventurous traveler, not the risk-averse.